#------------------------------------------------------------------------------
#$Date: 2017-11-15 14:59:14 +0200 (Wed, 15 Nov 2017) $
#$Revision: 203217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/31/2103109.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2103109
loop_
_publ_author_name
'Britton, Doyle'
_publ_section_title
;
 Planar packing of tetrachlorodicyanobenzene isomers
;
_journal_coden_ASTM              ASBSDK
_journal_issue                   3
_journal_name_full
;
 Acta Crystallographica, Section B: Structural Science
;
_journal_page_first              553
_journal_page_last               563
_journal_paper_doi               10.1107/S0108768102003348
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C8 Cl4 N2, C12 H18'
_chemical_formula_sum            'C20 H18 Cl4 N2'
_chemical_formula_weight         428.16
_chemical_name_systematic
;
 para tetrachlorodicyanobenzene/hexamethylbenzene, 1/1,
 polymorph II
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL plus manual additions'
_cell_angle_alpha                116.697(3)
_cell_angle_beta                 112.099(3)
_cell_angle_gamma                92.101(3)
_cell_formula_units_Z            1
_cell_length_a                   7.5567(11)
_cell_length_b                   8.8956(11)
_cell_length_c                   8.9921(11)
_cell_measurement_reflns_used    876
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      4.5
_cell_volume                     484.66(11)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'TEXSAN, SHELXTL'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1994)'
_computing_structure_solution    'TEXSAN, MITHRIL, DIRDIF'
_diffrn_ambient_temperature      174(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
 Siemens SMART arae-detector diffractometer
;
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5128
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_interval_time  '600 min'
_diffrn_standards_number         111
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  SADABS;  Sheldrick, 1996;  Blessing, 1995
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.311
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.067P)²+0.121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                1890
_reflns_number_total             2198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk0105.cif
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2103109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 -0.0078(2) -0.1001(2) -0.1743(2) 0.0292(3) Uani d . 1 C
C2 -0.0065(2) -0.1770(2) -0.0679(2) 0.0305(3) Uani d . 1 C
C3 0.0013(2) -0.0766(2) 0.1063(2) 0.0302(3) Uani d . 1 C
C7 -0.0196(3) -0.2039(2) -0.3571(2) 0.0337(4) Uani d . 1 C
N1 -0.0339(2) -0.2857(2) -0.5039(2) 0.0421(4) Uani d . 1 N
Cl2 -0.01561(7) -0.39377(5) -0.15658(6) 0.04022(16) Uani d . 1 Cl
Cl3 0.00284(7) -0.16577(6) 0.24079(6) 0.03724(15) Uani d . 1 Cl
C11 0.5086(2) 0.1775(2) 0.0652(2) 0.0358(4) Uani d . 1 C
C12 0.4922(2) 0.0703(3) -0.1139(2) 0.0365(4) Uani d . 1 C
C13 0.4848(2) -0.1067(2) -0.1783(2) 0.0363(4) Uani d . 1 C
C21 0.5203(3) 0.3698(3) 0.1377(3) 0.0507(5) Uani d . 1 C
H21A 0.4921 0.3946 0.0365 0.076 Uiso calc PR 0.50 H
H21B 0.6529 0.4373 0.2363 0.076 Uiso calc PR 0.50 H
H21C 0.4233 0.4017 0.1870 0.076 Uiso calc PR 0.50 H
H21D 0.5535 0.4278 0.2701 0.076 Uiso calc PR 0.50 H
H21E 0.3927 0.3851 0.0702 0.076 Uiso calc PR 0.50 H
H21F 0.6222 0.4207 0.1195 0.076 Uiso calc PR 0.50 H
C22 0.4800(3) 0.1460(3) -0.2385(3) 0.0500(5) Uani d . 1 C
H22A 0.5532 0.2684 -0.1620 0.075 Uiso calc PR 0.50 H
H22B 0.3417 0.1371 -0.3115 0.075 Uiso calc PR 0.50 H
H22C 0.5374 0.0813 -0.3222 0.075 Uiso calc PR 0.50 H
H22D 0.4017 0.0561 -0.3685 0.075 Uiso calc PR 0.50 H
H22E 0.6132 0.1874 -0.2190 0.075 Uiso calc PR 0.50 H
H22F 0.4174 0.2432 -0.2082 0.075 Uiso calc PR 0.50 H
C23 0.4692(3) -0.2219(3) -0.3704(3) 0.0511(5) Uani d . 1 C
H23A 0.4131 -0.3431 -0.4134 0.077 Uiso calc PR 0.50 H
H23B 0.6006 -0.2102 -0.3662 0.077 Uiso calc PR 0.50 H
H23C 0.3837 -0.1869 -0.4558 0.077 Uiso calc PR 0.50 H
H23D 0.5185 -0.1504 -0.4102 0.077 Uiso calc PR 0.50 H
H23E 0.3310 -0.2832 -0.4574 0.077 Uiso calc PR 0.50 H
H23F 0.5479 -0.3066 -0.3678 0.077 Uiso calc PR 0.50 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 C1 C2 2 . 120.54(14)
C3 C1 C7 2 . 119.38(14)
C2 C1 C7 . . 120.07(15)
C3 C2 C1 . . 119.56(15)
C3 C2 Cl2 . . 121.35(13)
C1 C2 Cl2 . . 119.09(12)
C2 C3 C1 . 2 119.90(15)
C2 C3 Cl3 . . 121.01(13)
C1 C3 Cl3 2 . 119.09(12)
N1 C7 C1 . . 178.19(19)
C13 C11 C12 2_655 . 119.97(17)
C13 C11 C21 2_655 . 119.65(16)
C12 C11 C21 . . 120.37(17)
C13 C12 C11 . . 119.86(16)
C13 C12 C22 . . 120.09(17)
C11 C12 C22 . . 120.05(18)
C12 C13 C11 . 2_655 120.17(16)
C12 C13 C23 . . 119.94(17)
C11 C13 C23 2_655 . 119.89(18)
C11 C21 H21A . . 109.5
C11 C21 H21B . . 109.5
H21A C21 H21B . . 109.5
C11 C21 H21C . . 109.5
H21A C21 H21C . . 109.5
H21B C21 H21C . . 109.5
C11 C21 H21D . . 109.5
H21A C21 H21D . . 141.1
H21B C21 H21D . . 56.3
H21C C21 H21D . . 56.3
C11 C21 H21E . . 109.5
H21A C21 H21E . . 56.3
H21B C21 H21E . . 141.1
H21C C21 H21E . . 56.3
H21D C21 H21E . . 109.5
C11 C21 H21F . . 109.5
H21A C21 H21F . . 56.3
H21B C21 H21F . . 56.3
H21C C21 H21F . . 141.1
H21D C21 H21F . . 109.5
H21E C21 H21F . . 109.5
C12 C22 H22A . . 109.5
C12 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C12 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C12 C22 H22D . . 109.5
H22A C22 H22D . . 141.1
H22B C22 H22D . . 56.3
H22C C22 H22D . . 56.3
C12 C22 H22E . . 109.5
H22A C22 H22E . . 56.3
H22B C22 H22E . . 141.1
H22C C22 H22E . . 56.3
H22D C22 H22E . . 109.5
C12 C22 H22F . . 109.5
H22A C22 H22F . . 56.3
H22B C22 H22F . . 56.3
H22C C22 H22F . . 141.1
H22D C22 H22F . . 109.5
H22E C22 H22F . . 109.5
C13 C23 H23A . . 109.5
C13 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
C13 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
C13 C23 H23D . . 109.5
H23A C23 H23D . . 141.1
H23B C23 H23D . . 56.3
H23C C23 H23D . . 56.3
C13 C23 H23E . . 109.5
H23A C23 H23E . . 56.3
H23B C23 H23E . . 141.1
H23C C23 H23E . . 56.3
H23D C23 H23E . . 109.5
C13 C23 H23F . . 109.5
H23A C23 H23F . . 56.3
H23B C23 H23F . . 56.3
H23C C23 H23F . . 141.1
H23D C23 H23F . . 109.5
H23E C23 H23F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C3 2 1.398(2)
C1 C2 . 1.402(2)
C1 C7 . 1.443(2)
C2 C3 . 1.387(2)
C2 Cl2 . 1.7106(16)
C3 C1 2 1.398(2)
C3 Cl3 . 1.7163(16)
C7 N1 . 1.144(2)
C11 C13 2_655 1.405(3)
C11 C12 . 1.407(3)
C11 C21 . 1.518(3)
C12 C13 . 1.403(3)
C12 C22 . 1.524(3)
C13 C11 2_655 1.405(3)
C13 C23 . 1.515(2)
C21 H21A . 0.9800
C21 H21B . 0.9800
C21 H21C . 0.9800
C21 H21D . 0.9800
C21 H21E . 0.9800
C21 H21F . 0.9800
C22 H22A . 0.9800
C22 H22B . 0.9800
C22 H22C . 0.9800
C22 H22D . 0.9800
C22 H22E . 0.9800
C22 H22F . 0.9800
C23 H23A . 0.9800
C23 H23B . 0.9800
C23 H23C . 0.9800
C23 H23D . 0.9800
C23 H23E . 0.9800
C23 H23F . 0.9800
